Becoming Melissa’s Cuckold


My name is Grey, I’ll withhold my last name for reasons that will become obvious as my story unfolds. I was a bit of a nerd in high school. I wasn’t really picked on or anything like that, but I was shy, kept to myself and didn’t have a lot of friends. In my graduating year I became close friends with a girl named Melissa. She grew up in the city, but her parents were going through a separation and they’d sent her to live with an aunt in the suburbs while they sorted things out. Melissa wasn’t just from the city, she was the epitome of a “big city” girl. She was mature way beyond her years, very cultured and far ahead of the rest of us in the suburbs. She was into things like art and fashion and knew about all sorts of cool underground music that none of us had ever heard of before.

Needless to say, Melissa stood out like a sore thumb in our quiet suburb and intimidated pretty much everyone. Some of the popular jock guys at school tried to pick her up, but she shot them down in a hurry. Her downtown friends were the in-crowd trendsetters, they were artists or in bands and hung out at the type of clubs that no one else could get into. There was no way that some high school football player was ever going to impress her. Melissa and I bonded over the most simple thing – people were too afraid to talk to her, and no one bothered to talk to me. We were loners for different reasons, but managed to find a connection because of that.

We became very close over during our senior year. Of course I was madly in love with her, but I knew that she was way out of my league. I was a decent looking guy, but didn’t have the confidence to match so I always considered myself to be average in every respect. Melissa was a stunner. She was petite, had blond hair and an hourglass figure topped off by breasts that only a girl that age could have and the most perfect ass I’ve ever seen in my life. I wanted more from her but knew that was never going to happen between us. I felt lucky just to be her friend.

As the school year came to an end, we started talking about the future. By then her parents had divorced and Melissa was preparing to move back to the city. She didn’t want to live with either parent and was thinking of getting a place of her own, but to make it work she’d need a roommate. I wasn’t sure what my plans were. I wanted to go to college, but I was one credit short of graduating high school. Melissa convinced me to move in with her and laid out a plan for me. She knew of an alternative school where I could go part time and get the credit that I needed to graduate and one of her friends was willing to hire me on at a printing press that he owned. She created a budget for me that showed even after paying rent and other expenses I’d have enough money for my first year of college as soon as I got the last credit that I needed. I didn’t realize it at the time, but this was an early sign of Melissa’s controlling ways when it came to me.

The first few months that we lived together was a blur for me. I got to know all of Melissa’s friends and started hanging out at all of the cool clubs. The high school nerd that I was just months ago was now walking to the front of the line at the most exclusive clubs in the city. I’ll never forget the first time that I walked passed a group of football players and cheerleaders from my high school who couldn’t get into the club that I was now a regular at. I just passed them by as I went to the front of the line and got waved in by the bouncer. The looks on their faces was priceless!

As much as I felt accepted for the first time in my life, there was always a bit of a feeling that these were Melissa’s friends – that I was who I was because of her. I was having too much fun to really be bothered by it, and I figured over time I’d make my own friends in this same circle and find my own way, while always being grateful to Melissa. I’d changed almost everything about myself – new clothes, new haircut, new confidence and I knew I owed it all to Melissa. I’d spent my whole life feeling ‘average’ and suddenly I felt like I was somebody. I left the old version of me behind in the suburbs and discovered a new me in the city.

As much as I learned about myself during that time, I learned even more about Melissa. She was far more wild than I ever could have imagined! I knew that she liked to party, but I had no idea to what extent! She was sex, drugs and rock’n’roll personified. I’d still been holding out hope that maybe I’d have a chance with her somehow, but it became more clear than ever that was never going to happen. I didn’t judge her at all for it at all, but Melissa had a lot of men in her life. I don’t want to sidetrack from my own story, but two members of Metallica came to blows over Melissa! That’s the type of girl she was. She’d often bring guys back to our place and I’d listen to her marathon sex sessions through the thin wall that separated our bedrooms. I knew that there was no way that I could ever compete with these guys.

Which brings me to my next point. I was 19 and still a virgin. I was really embarrassed about it and kept it a secret. None of my new friends were virgins. They were as wild as Melissa was, most of them had lost their virginities long ago. And that was my problem. I’d had opportunities to get with some of the girls that I’d met through Melissa, but I was too intimidated to do anything with them. They all seemed so mature and so experienced. Literally hearing how guys fucked Melissa and hearing similar stories about our other friends, I was not only afraid that I’d be a disappointment – I was also afraid that I’d lose part of the cool new image that I’d built up for myself.

Melissa was the only one of our friends who knew that I was a virgin, and felt sorry for me. When she found out that I had a crush on her friend Victoria she hatched a plan to get the two of us together.

Victoria was a little more modest than the rest of our group and seemed a little less experienced too, she at least spoke less about the men in her life than the others did. Maybe that’s why I liked her so much, but it didn’t hurt that she was absolutely gorgeous too. Victoria was tall, brunette and had a slender model-like figure, which worked out well for her because she was a model. Before I’d met her or even knew that she as from the same city as I was, I’d seen her on billboards and poster sized ads in the subway. I couldn’t believe it when I met her – it felt like I was meeting a celebrity – and really couldn’t believe that she was more beautiful in person than she was in print. I was incredibly intimidated by Victoria, but she was a really nice girl and because of that the most approachable of Melissa’s friends. I figured that maybe her looks scared other men away or something. When we went out as a group she’d often find her way over to me and we spent a fair amount of time together and had quite a lot in common. For one thing, she was a bit of a late bloomer too.

Melissa’s plan to hook us up was pretty simple – she’d talk me up to Victoria and open her up to the idea of dating me, while also coaching me up and give me the skills that I’d need to impress Victoria.

Knowing that I was a virgin, one of Melissa’s first bits of advice was to try to control myself when I masturbated. I was at an age when I still denied that I masturbated, but Melissa was having none of that. “I bet you jerk off every time you hear me getting fucked!” Although I didn’t admit it, she was right. She taught me about ‘edging’ – masturbating to the point of orgasming, but stopping before there was a release. She told me that if I ever got with Victoria, I couldn’t be a “two pump chump” and needed to learn how to control myself. It made sense to me, and I had a tendency to do whatever Melissa told me to do anyway.

It was very embarrassing for me at the time, but for the next few weeks Melissa spent a lot of her time focused on my masturbation habits. She wanted to know when I masturbated, how often I masturbated and how long I was able to delay my orgasms for. I’ll be honest, I was a 19 year old virgin living with an overly sexual beautiful woman so I masturbated a lot! I was doing my best to work on prolonging myself, but orgasm control wasn’t the easiest thing for me to learn. Melissa kept a chart of my habits, but I lied to her. I wasn’t honest about how many times I jerked off and I exaggerated how long I could control myself for.

During this time, Melissa was subtly warming Victoria up to the idea of going on a date with me. She didn’t come right out and say it, but was always sure to say something nice about me to her and pointed out how I wasn’t like the other guys who’d let her down in the past. We continued to go out socially as a group and I made sure to talk to Victoria, make her laugh and feel comfortable around me – all tips from Melissa’s coaching.

After a few weeks, Melissa convinced me that Victoria would say yes if I asked her out. It was the first time that I’d ever asked a girl out on a date and I was incredibly nervous. There was a band coming to town that I knew Victoria liked. I got a pair of tickets and casually mentioned to her that my ‘friend’ backed out and I needed to find someone else to go with. “I’ll go!” she said with excitement, maybe more for the band than me but it was a yes and that’s all I wanted to hear!

In the days leading up to our date, Melissa was drilling me with advice – what to do, what not to do, how to act, how not to act, where to go before the show, where to take her afterwards. It was like a crash course in dating. While I was absorbing everything that she was saying, it was also a bit of a reminder of how little I knew about dating.

As the day of our date approached, Melissa brought up the subject of orgasm control again.

“Your chart says that you can jerk it for 45 minutes without cumming now” – which was a lie – “that’s a huge improvement from when you first started”

“I’ve been focusing on getting better” – a semi lie, I’d been trying but was nowhere near that successful.

“Before I let you go out with Victoria, I need to know. I can’t let you embarrass me – or yourself for that matter.”

“Know? Know what?”

“How long you can last.”

“You do know – look at the chart, 45 minutes”

“No, I need to see it for myself”

“Are you saying that you want me to jerk off for you?”

“Yes, it’s for your own good. Even if you can wank it for 45 minutes – and we’ll see about that – you’ve never seen a naked woman before, never touched a girl, never shown anyone your dick before. All of your training is going to go out the window if you’re all nervous. Pull it out for me, show me what you can do with a woman in the room.”

“Melissa, I’m not going to do this.” I was trying hard to cover up the fact that her frank talk was giving me an erection.

“If you’re not going to do this, you’re not going out with Victoria. It’s as simple as that Grey. Don’t think I can’t call the whole thing off.”

I knew that she could.

“We’re going on a first date Melissa, we’re not going to have sex.”

“Yeah, but with everything that I’ve taught you this one date will lead to two, then three. It will happen faster than you think. I’m not going to let this get off the ground unless I’m sure that you won’t make a fool of me by cumming in your pants as soon as she touches you.”

I stood there confused, trying to think my way out of the situation.

“I can see your boner through your pants. I know that you want to jerk, just do it. Do it if you want to go on that date with Victoria. I’m going to count to 10. When I get to 10 I’m either going to see you with your dick in your hand, or I’m calling Victoria and telling her the date is off. 1…2…3…4…”

And in that moment, I made a decision that changed things forever for me. I quickly undid my pants, pulled them down and slid my hand into my boxer-shorts. I grabbed my cock and started stroking.

“Underwear too, I want to see it all.”

I was nervous, but already committed to this. I pulled down my underwear and stood naked form the waist down in front of a beautiful woman for the first time in my life. I saw a bit of a smirk and maybe a smile cross Melissa’s face as she looked at my cock – did she laugh? She looked me in the eyes and with a devilish look on her face she said “stroke”.

I stood there harder than I’d ever been and began stroking my cock with more intensity than I ever had before. I was ready to cum within seconds and struggled to distract myself. I looked down at floor knowing that if I looked at Melissa it would put me over the edge. She had no mercy.

“Look at me” she said and I slowly tilted my head up from the floor. Melissa was grinning ear to ear, clearly enjoying my predicament. “Tell me what you’re thinking about. Are you thinking about sliding your cock into Victoria’s tight little pussy?”

And with the image conjured up by that one sentence my cock exploded and I shot jets of cum all over the place, including on to the bottom of one of Melissa’s pant legs. I wish that I had more time to enjoy the best orgasm of my life, but I was shocked back into the moment with Melissa yelling “GET IT OFF OF ME, NOW!”

It became a bit of a comedy, me fumbling around with my pants around my ankles, hand still covered in cum trying not to touch anything and Melissa screaming at me.

“Don’t worry about your pants, get a towel and clean me the fuck up now!”

I stepped out of my jeans leaving them behind and half naked ran to the bathroom to get a towel. I came back to our living room with Melissa still standing there with a furious look on her face. I got down on my knees in front of her and began to wipe away my cum from her pants.

“The floor too, don’t let that shit stain the hardwood floors!”

With everything finally cleaned up and the towel in the wash, I sheepishly made my way back to the living room.

Melissa was now sitting on our couch with my pants and underwear at her feet. I bent over to grab them and she moved her foot on to them preventing me from picking them up. “Stand up” she said. I did, and instinctively use my hands to cover myself up.

“Do you think after a performance like that you’re ready for a woman like Victoria?”

“I hadn’t masturbated today…”, I tailed off sensing that she could tell that I was lying. “You’re making too much of this. It’s just a first date.”

“No it’s not, there’s no way you’re going out with her. I’m not going to let you embarrass me. Move your hands, I want to see your dick.”

I stood there frozen and somewhat humiliated.

“Move your fucking hands” she said with emphasis on each word.

As always, doing what she told me to do I moved my hands to my side.

“You know Victoria is a model, right?”

“Yeah…” I said not sure what she was getting at.

“I know that you’re a virgin, but I thought when you set your sights on Victoria that it meant that you had at least a decent sized cock in your pants.” Pointing at my dick, “That, that’s not enough for a woman like her. She’s not going to want that. She needs a real man’s cock, that’s a boy’s penis. Haven’t you noticed when she’s mentioned guys before that they’ve all been black?”

I hadn’t until now, but as soon as Melissa mentioned it I realized that she was right.

“I’ve spent nearly a month trying to convince her to try dating a white guy for once because I stupidly assumed that you knew what was up and had the goods. It was a challenge knowing that you were a virgin, but I was hoping that with a decent sized cock she’d have a little fun breaking you in. I can’t set her up with that” she said pointing to my penis with a sense of disgust in her voice.

All of my new found confidence that had been building up for months came crashing down around me, what was happening? I’d become aware of Melissa’s controlling side before this, but this mean streak was new to me. It was impossible to not realize that the nature of our friendship was changing in that very moment.

“Take your clothes and go to your room”

I did as I was told.

From my bedroom I heard Melissa on the phone “Hi Victoria? Good news/bad news. Grey can’t make the concert on Friday but I’ll be using his ticket. We can go together, maybe afterwards we can hit the club and pick up a couple of guys!”

I sat alone in my room trying to make sense of everything. It was a very confusing time for me. In the year or so that I’d known Melissa I went from being a suburban high school nobody to being part of the cool clique in the city. It was an incredible rebirth for me. And in the last half hour all of that felt like it had been washed away. My confidence had been replaced by insecurity – was my penis really that small? I’d never thought so but hearing it said out loud had me doubting myself. On top of that, I had no idea where my friendship with Melissa stood any more. Was she going to kick me out? Was she going to banish me from her circle of friends? Was I going to head back to the suburbs with my tail between my legs?

I barely slept that night with all of those questions running through my head, but I’d start getting answers as soon as the next day.


The next morning I was both afraid and embarrassed to leave my room. I didn’t know how I was going to face Melissa and I was worried about how things were going to change between us.

As I lay in bed worrying about these things, there was a knock at my bedroom door.

“I’m coming in” Melissa informed, not asked. There was an awkward moment between us, but she came over to my bed and sat on the edge.

“Listen, I’m sorry about last night. I was harsh and I shouldn’t have been. It’s just that I put so much work into trying to get you and Victoria together and when I realized that my time was wasted I got angry.”

I was still embarrassed, but I felt the sincerity in her voice.

“You know that I’m new to all of this, I didn’t know about Victoria’s…’preference’, it didn’t occur to me at all. It’s not something that I even thought to think about. I was so worried and focused on the little things…”

“Not ALL the ‘little things'” she joked glancing down towards my penis.

I turned beet red.

“Aww, I’m sorry. It was just a little joke. Oops, sorry I didn’t mean ‘little’ joke, I meant silly! It was just a silly joke!”

“It’s not funny!” I said probably revealing my bruised ego.

“I’m trying to apologize here, don’t get pissy with me! Listen, I’m sorry about last night. In my defense, I worked so hard to set things up with Victoria and I was so happy for you! My virgin friend from high school was going to get his first bit of pussy, and it was going to be with a model no less! And then you dropped your pants I knew that I’d been wasting my time. I was furious and my anger got the best of me. Anyway, I’m sorry and I hope we can still be friends?”

“Of course Melissa! I owe you so much and I want to thank you for everything that you did to help me, not just with Victoria but everything since we’ve been friends. Don’t feel too bad about me not losing my virginity though, as I said last night it was just a first date – it’s not like we were going to do it.”

“Actually, you were.”


“I kinda mighta told Victoria that you were a virgin.”

“WHAT? Who else knows?” I was in a bit of a panic.

“Calm down, just Victoria. I had to tell her so she took it easy on you and didn’t ‘spook’ you being as aggressive as she normally is. She’s never been a guy’s first and thought that it was hot. She was totally going to fuck you after the concert. Her parents are at the cottage for the weekend, you probably would have been getting it all weekend long.”

My heart sank thinking of the possibilities and missed opportunity of a lifetime.

“Well, maybe it’s not too late…if she thought it was hot then maybe she’d still be into it…” I was scrambling.

Melissa looked down towards where my groin area was under the sheets. “No Grey, it’s not going to happen. Not now, not ever. Not with her.” she said matter of factly.

The realization was crushing to me. I can’t believe that I had a chance to have sex with one of the most beautiful women I’d ever seen in my life. Not only was that not going to happen, but now she also knew that I was a virgin. I was going to be embarrassed around her and have to worry about her telling our other friends too.

Melissa interrupted my thoughts.

“As much as I am sorry, you need to understand that wasn’t trying to be mean to you Grey. I’m actually looking out for you. Isn’t it better that what happened last night happened between us and not between you and Victoria? You would have been SO humiliated if you pulled that thing out for her. A normal girl would have been put off, but Victoria is used to huge black cocks. She was willing to go with you being a virgin, but a small penis too? No way. She assumed you must have had a big cock, we both did – why else would you go for a girl like that? However embarrassed you were with me, trust me – I saved you from much worse from her.”

“I suppose so.” I paused to reflect for a moment. “I thought that she was such a nice girl though, she seemed different from the others.”

“She is a nice girl, don’t judge her because she loves big cocks. Just because she’s nice doesn’t mean that she doesn’t want to really feel it when she’s getting fucked. Being a size Queen and nice aren’t mutually exclusive, Victoria is both.”

I was afraid to ask but couldn’t prevent myself. “Is mine really that small?”

“Well, it’s not tiny but umm…it isn’t exactly big either.”

“Average?” I asked hopefully.

“No, it’s smaller than average. It’s “cute”. That’s better than gross, right? Maybe one day you’ll find a woman who doesn’t mind little penises or something?”

“Why are you calling it my ‘penis’ now? When you were charting my orgasm control you always called it either my ‘cock’ or my ‘dick’, but since you saw it last night you’ve only referred to it as my penis. How come?”

“Huh, I didn’t notice really. It’s subconscious I guess. ‘Cock’ is something that I crave, I want ‘cock’. I want to get fucked by a ‘cock’. I want to suck a ‘cock’. I associate ‘cock’ with something that I lust after. In my mind ‘cocks’ are big. ‘Dick’ I guess is average. You know, like sometimes if a guy is cool I’ll suck his ‘dick’ or let him stick his ‘dick’ in me. Penis is something else, like non-sexual. There’s nothing really desirable about a ‘penis’, it’s just a thing. No woman has ever said “I can’t wait get rammed by that penis”. Penises are just kinda there, definitely not for fucking.”

I think that Melissa’s mind drifted a bit as she got caught up in her answer to my question and forgot that she was actually talking about me before she snapped back to the present.

“Oh but umm, like I said I’m sure that some girls don’t mind penises. I’ve also heard that sex isn’t all that important to some women, like a churchy girl or something?”

Her attempt to make me feel better fell flat.

“Or maybe you can get a penis pump, maybe they work?” After pausing for a minute she added “Notice how it’s not called a cock pump or a dick pump? It’s the penises that need the help!”

It was another blow to my ego, but I had to laugh.

Over the next few weeks, things more or less returned to normal between Melissa and I. The one most notable change was how much more open she was about talking about her sex life with me. She was never exactly shy about it, but now she was going into detail like she never had before. When we went out to the club we played a game she called ‘Cock or Dick’. She’d point out a guy that she’d slept with and I had to guess if they had a cock or a dick. She didn’t have sex with penises so that was never an option. Often playing the game would end up with her telling me all out her encounter with the guy and after I while I realized that was the true purpose of the game. It was an excuse for her to tell me about her wild fuck sessions with all these different guys. Other times when she brought a guy home it became a regular morning-after ritual for her to tell me all about what they’d done the night before – as if I hadn’t been listening to them and beating off the whole time. I eventually asked her why she was suddenly more expressive about her sex life with me.

“Well, now that I know about your penis situation I figured that sex for you is probably just going to be masturbation – not real sex – so I’m trying to help you out, give you something to think about when you whack it.”

She was pitying me, and the worst part was that it was I needed it. My favourite times to masturbate were either when I listened to her fucking a guy in the room next to me, or the following day after when she’d tell me all about it. I’d let her give me all the juicy details then wait for what I thought was a respectable amount of time after our talk and head to my room and jerk off. Apparently I hadn’t been as subtle as I thought that I was.

“You’re blushing!”

She could see how embarrassed I was. Not only that, but her words about how sex for me was going to be masturbation hurt, because I had a deepening feeling that she was right. I was approaching 20 years old and was still a virgin. It hadn’t happened for me yet, and that was before I had a complex about having a small penis. Finding out that the girls in our circle of friends expect a big cock made it all the worse for me. I hadn’t even attempted to approach a woman in a club since Melissa opened my eyes to my little problem.

“Oh come on, don’t be all shy about it. You masturbate instead of fuck and I try to help you out by givng you things to think about when you’re doing it. That’s a good thing isn’t it? I mean the me helping you part, not the you not fucking part. That part is sad.”

“Melissa! You’re not helping!”

“I am, you’re just too embarrassed to admit it. You’re all embarrassed because you’re uncomfortable, but you wouldn’t be uncomfortable if you didn’t always try to hide things. Tell you what, why don’t you pull it out and give it a tug right now?”

“Melissa, I’m not going to masturbate for you.”

“You did it before and I saw the load that you shot, you can’t tell me that you don’t want cum like that again! Trust me, it will be good. Pull it out and stroke it for me.”

“No Melissa” I wanted to do it so badly. Just the thought of stroking it for her was getting me hard, but I also didn’t want to risk more humiliation. I had to stare at the floor to avoid her charms.

“I can see your stiffy through your pants, stop acting like you don’t want to. It will feel good, stop denying yourself. It’s ok!”

Melissa really knew how to tempt me, she also knew I always ended up doing what she told me to. It was only a matter of time.

“Listen, we both know that you’re going to give it a tug today, at least once right? What’s more exciting, you alone in your room hiding under the covers trying to convince yourself that I don’t know what you’re doing or pulling it out right here in front of me? Look at me Grey”

I looked up at her. I knew I was doomed.

“I know how hard I can make you cum. I want to make you cum. Pull your penis out, now” she said firmly but reassuringly.

I gave in. I stood up and undid my pants, and reached my hand inside.

“No, I want see it. Do it properly, pants off, underwear off.”

I did what she said and stripped down, fully exposing myself.

“Good boy” she said with a smile. I stood facing Melissa as she sat on the couch in front of me “start” she said.

I began stroking my penis for her. Unlike last time, I fought the urge to look away from Melissa. It was embarrassing, but it also felt so good! I was thinking about the sex she had last night. I masturbated in my room while I listened to her getting fucked the night before, but now I was in the room with her and I imagined what it would be like to fuck her.

“That’s it” she said with a smile, licking her lips slowly and seductively.

“You’re thinking about last night aren’t you, the fucking that Richie gave me?”

“Yes” I admitted.

“You played with yourself last night too, didn’t you?”

“Yes” I repeated still stroking.

“I know you heard us fucking, but before that could you hear me sucking Richie’s cock? Did I slurp it loud enough for you do hear?”

“Yes, I heard everything”

Melissa smiled at me “Good, because I was trying to be loud for your benefit. I knew you’d be tugging away on your little guy – just like you are now. When did you cum Grey? Did you cum when I was sucking on Richie’s cock or did you make it until he fucked me?”

I was honest “I came listening to you give him head”

She looked proud of herself. “Was it a big load?”


“You’d like a blow job, wouldn’t you?”

“Yes” I said again, my knees buckling at the thought of it.

“Look at my lips Grey, imagine if you had a real cock and my pouty lips were wrapped around it, sucking it and slurping on it like a greedy slut.”

I didn’t like her making fun of my penis, but I was too excited to try to stop any part of what was happening.

“Imagine me down on my knees in front of you, desperate for your cock, my eyes looking up at you begging. ‘Can I suck your cock?’ ‘Please, I need it in my mouth.’ ‘Pleeeease let me suck your cock, I’ll to anything if you just let me suck your cock please?’ ‘I’m so hungry, please feed it to me'”

My penis was throbbing. Melissa’s words to me now echoed what I’d heard her say to Richie last night. She smiled watching me stroke, enjoying the effect she was having on me.

“When Richie left here this morning, my lip stick was smeared all over his cock. He had one more load to give me so I sucked him off again before he left. He doesn’t have to imagine anything Grey, he knows. Don’t you wish that you had a big cock like Richie’s? Then you wouldn’t have to imagine it, you’d know too. If your penis was as big as his cock I’d suck it right now.”

That was it for me and like last time I shot a giant load all over the place. Arches of cum shot from my penis as my knees gave out and I nearly fell over. This orgasm was better than the last one I had in front of her, and I hoped that the next one would come a lot sooner.

“Wow! Nice load! Hurry though, clean it up!”

After cleaning things up, Melissa called me back into the living room.

“That was a good orgasm, wasn’t it?”

“Honestly, the best I’ve ever had”

“Awesome! I’m glad you said that because I wanted to propose something to you.”

“What’s that?” I asked.

“I think it would be best if you only masturbated when you do it for me. No other time, ever. Not matter what.”

It came across as more of a demand than a proposal.

“From now on, I don’t want to see your bedroom door closed and no more long showers. It’s for your own good. Masturbation is sex for you virgin boy, and I don’t want you to ruin it by doing it too much. We’ll make it special for you this way. This means no more stroking it when I’m not around, and no more stroking it when I’m getting fucked either – you wait for the next day and do it for me.”

I didn’t want to tell her how much I didn’t want to give that up, but these orgasms that I was having with her were the best I’d ever had and I wanted more like this.

“Think about it, from here on out our sex lives will be linked. Every time a man fucks me, you’ll get to put on a little stroke-show for me the next day. Whenever I have real sex, you get to have your version of sex the next day. That’s kinda hot, isn’t it? I don’t know of any other virgins who are that lucky. Mind you, I don’t actually know any other virgins haha!”

As usual, Melissa had a point. As much as I liked to masturbate, I probably did it too much on my own and it was always better when Melissa was involved. I’d really miss stroking to the sound of her getting fucked, but if it meant doing it in front of her and cumming like I just did it might be worth trying. Besides, she had sex often enough where I’d still get to cum quite a bit – and maybe I could talk her in to some bonus sessions or something.

“Ok” I agreed, not really feeling like I had much of a choice. That was the nature of Melissa’s control over me.

“No cheating” she said “If I see a little load shoot out of your penis I’ll know what you’be been up to without me and I won’t be happy.”

And from that day forward there was a new rule in our house. I was only allowed to masturbate if Melissa watched. She definitely made it worth my while. The intensity of the orgasms that I had performing for Melissa were way more powerful than when I was on my own. Melissa had fun with it too. She kept trying new ways to excite me and made mental notes of anything that she did or said that made me shoot a bigger load than usual. This is how I discovered a fetish that I didn’t know that I had, and one that would change the nature of our relationship once again.


For the first few weeks after coming to an agreement about my masturbation habits with Melissa things worked out fairly well. I was masturbating much less than I had been before, but Melissa was right – by doing it with her and for her it was much better. Even though I wasn’t having sex with her at all, it felt like we had a sexual relationship because so much of my sexual energy was tied up in her. When we went out clubbing, I was excited when she’d meet a guy and I’d hope that they would hit it off. I knew that if things went well with them and she brought the guy home with us that I would be rewarded with a great masturbation session the following day. It’s a strange thing to say, but this really brought us closer together. It was a secret game that only the two of us knew about.

I also have to admit though that I wasn’t always faithful to our agreement. I wanted to be and tried to but there were times when Melissa wasn’t around and I really needed a release.

And this is how I discovered a fetish that I didn’t know that I had.

One day a few weeks into our agreement I was home alone and really needed to cum. It was around lunch time and Melissa wasn’t going to be home for quite a few hours. Even if I could wait for her I didn’t think that she would be in the mood for me. Earlier that morning we’d gotten into an argument over keeping the kitchen clean and when she left for work she was still angry with me. I wasn’t exactly expecting her to come home all sunshine and smiles after our morning blow out – that girl knew how to hold a grudge.

I decided to take care of myself, left our living room, headed to my bedroom and stopped off at our bathroom to grab some tissues. When I got to our bathroom I grabbed the box of tissues and as I turned to leave I noticed Melissa’s clothes piled on the floor in the corner. How ironic that she freaked out on me for leaving my dishes in the sink, but here she was leaving her clothes on the floor of our bathroom. I took a couple of steps towards the door when I stopped. I really don’t know what came over me, but without much thought I reached down into the pile of Melissa’s clothes and found her panties. I guess maybe I wanted to feel close to her in some way when I jerked off or something, but I knew that on that day when I shot my load it was going to be into her panties.

When I got to my room I laid her panties down on my bed. I stared at them in awe. Knowing that these panties were worn snug to Melissa’s pussy was so exciting to me. My penis got rock hard and I stroked myself just looking at them, almost worshiping them – maybe even jealous of them because they’d been so close to where I wanted to be. I knew that I wasn’t going to be able to last long and in my drunken lust I picked Melissa’s panties up, smelled them and then wrapped them around my penis and stroked myself to an intense orgasm.

I ended up cleaning our whole apartment. I told Melissa that it was to apologize for leaving the kitchen a mess earlier, but really it was to cover up my perversion. Her panties were covered in my cum and I needed to do her laundry to hide what I’d done.

Doing this became a bit of a thing for me. My preference was still to masturbate in front of Melissa, but when she wasn’t around her panties became a nice substitute for her. I’d either find a pair in her laundry hamper or if there weren’t any there I’d go into her panty drawer and get a pair from there. I had to be really careful when I did that, she wasn’t expecting them to be dirty so I couldn’t cum in them and had to put them back exactly as I’d found them.

I thought that I was pretty careful, but I eventually got caught and like some of the other events that I’ve shared, it changed everything for me and ultimately became how I was introduced to the idea of cuckolding.

Usually Melissa would bring home a guy on a Friday night after being out at the club, which meant I’d get to have my special time with her Saturday morning. Those weren’t the only times when I was allowed to jerk off, but they were the best times and the times that I looked forward to the most. It had been two days since I’d been allowed to masturbate for Melissa and I was really looking forward to our Saturday stroke session together. Unfortunately, on Thursday Melissa’s mum called with some bad news. She’d had a fall, badly sprained her ankle and wanted Melissa to spend the weekend at her place while she got used to her crutches. Realizing what that meant for me, I stupidly tried to talk Melissa into letting me jerk off for her before she left for the weekend.

“Are you fucking serious?”

The anger in her voice made me immediately regret asking.

“My mum is in pain and I have to give up my weekend to go be with her and all you care about is tugging your little penis?”

“I’m sorry Melissa, I didn’t mean for it to come across like that. Of course I’m concerned for your mum and I know it sucks that you won’t be able to go out this weekend. I just thought that…” I gave up mid-sentence realizing that there wasn’t anything I could say that wouldn’t make me sound selfish.

“It’s two days”

“I know, it’s just that it’s been two days so this will be two more days” I said, probably sounding sulky.

“Wow, four days without jerking off, how will you survive?” she said dripping with sarcasm.

I dropped the topic knowing that once she was gone I’d be able to dip into her panty drawer and get the release I wanted, which I did pretty much as soon as she’d left.

On the Saturday night that Melissa was gone, I faced a bit of a dilemma. I wanted to jerk off again – I had no self-control when I had such easy access to Melissa’s panties – but she’d be home the next day and would realize that I’d been masturbating behind her back if I didn’t shoot a big load for her, especially when she thought that I hadn’t jerked off in four days.

I was worried about how I’d explain it to her, but I couldn’t control myself. I gave into temptation, went into her bedroom and found a pair of panties in her laundry hamper. Instead of taking them back to my room, I decided to masturbate in Melissa’s room. I’d never done that before, but the idea of it added to the thrill of what I was doing. I took my pants off and laid down in Melissa’s bed. I held her panties with one hand as I stroked away with the other, thinking about all of the times that I’d heard Melissa getting fucked in the very bed that I was now laying in. As I was getting ready to cum I draped her panties across my face, placing the crotch right over my nose. I was stroking furiously, lost in my dream world building up to my orgasm when I was suddenly interrupted.


My heart sank. Not only had I been busted, but it wasn’t Melissa’s voice. It was Victoria’s – the model who I’d had a crush on months ago.

“Melissa, get in here!” Victoria shouted.

I scrambled in horror to put my pants on and toss Melissa’s panties into the laundry bin – the whole while watched by Victoria.

Within seconds Melissa was standing at the door to her bedroom too. There was no getting out of this situation. It was painfully obvious what I’d been doing, and I was terrified about our friends finding out about this.

“He was sniffing your panties Melissa!”

“What?!” she said.

“He had your undies on his face and he was jacking off!”

“I can explain!” I said but really, I couldn’t.

“You little fucking perv” Melissa scorned. “Get out! Get out of my room!”

I’ve never been more humiliated in my life. As I walked passed the girls, Melissa wound up and punched me in the back and followed that up by kicking me in the ass. That she was furious was obvious but I noticed that Victoria seemed to think that it was a bit funny. While Melissa was red with anger, Victoria had a bit of a smile on her face.

I couldn’t believe the mess I was in. I needed to try to explain things to Melissa, but there was no way that I could talk to her while she was in the state that she was in. I also needed to talk to both of the girls before they spoke to anyone else. I’d be a laughing stock if this got out.

I could hear the girls talking in our living room. I strained to hear what they were saying but really couldn’t make anything out. I just prayed that they weren’t on the phone with any more of our friends.

After an hour or so I head Victoria call me from the living room.

“Grey? Come here we want to talk to you.”

I was terrified of what was about to happen, but I knew that I needed to try to smooth this over as best as I could before the girls spoke to anyone else. With my head bowed, I left my bedroom and walked down the hallway towards our living room. Glancing up I could see Melissa and Victoria sitting side by side on our couch.

Melissa broke the silence.

“What do you have to say for youself?”

“I’m really sorry Melissa, I couldn’t help myself.”

I wanted to remind her that I hadn’t masturbated in 4 days – or so she thought – but I struggled to say anything at all with Victoria in the room. Perhaps sensing my hesitation Melissa spoke up.

“Don’t be shy in front of Victoria. I told her everything and I mean everything. You should actually start by thanking her. I was ready to kill you, but Vic calmed me down and made me realize a few things.”

“Aww, he’s turning red” Victoria giggled.

“I’m really sorry” I was repeating myself but didn’t know what else to say.

“So how long have you been sniffing my panties and jerking off behind my back?”

I ignored Melissa’s question, instead turning to Victoria. “You’re not going to tell anyone about this are you?”

“That depends,” she said. “Answer Melissa’s questions to my satisfaction and I could probably keep my mouth shut about what happened here tonight.” Victoria was clearly enjoying the moment.

With that I turned my attention back to Melissa.

“Not long, I swear. It only happened a few times” I lied, still embarrassed that I’d done it at all.

“How long is ‘not long’?”

“Just a couple of weeks, it was only a few times, I swear.” It had been closer to two months, and I’d done it at least 10 times – probably more.

“You fucking perv.” Maybe I was wrong, but I thought I saw Melissa crack a bit of a smile. She seemed less angry and was more interested in humiliating me, especially in front of Victoria.

“Melissa, remember what we talked about,” Victoria almost sounded like she was scolding Melissa.

“You’re right Victoria. Grey, I’m not really mad at what you did. It’s actually kind of hilarious in a really pathetic and creepy way. But I am mad that you cheated on me and I feel let down by that. I thought our ‘fun time’ together meant something to you.”


Continued on the next page (link Below)

One comment

  • GK

    I absolutely loved this story. The way it evolved the control the natural way the upper hand was always Melissa’s the involvement of the best friend who fucks BBC. The way as her best friend she could never allow her to date him because of his small cock because it would embarrass their girl friendship. Girls absolutely do look out for each other in that way and they do discuss male sizes. Any many who doubts that is an idiot… women talk!. I loved the way the therapist pinned down the selfishness of Grey and how she was able to ‘suggest’ a way forward for them BOTH… as the reader you know Grey is being set up from the moment he crossed the threshold into that Couples Therapy. I would love to read more.


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